I don't typically think of myself as someone who has a problem asking for help. As a short person, I'm always asking tall people for help. I also have to ask for help when I'm working. Handling a dangerous animal, working fast to save a life, you learn to ask for help for everyone's sake.
I'm not too bad at asking for help from my husband or son either, but when it comes to other people, I'm less likely to ask for help. I tend to feel guilty, or know that other people are just as busy, or busier than I am. I like to offer to help others. My husband often sees how my effort to help others will sometimes put our life off track momentarily, but I like to think of it as happy chaos.
A friend of ours last night asked if we could pick up her son, ( a good friend of my son from school) as she had an unexpected meeting. She was apologetic. I told her, "Why don't we pick him up and keep him for a playdate? My son would love to have a playdate with him." This worked out well and his Mom is getting to work uninterrupted this afternoon. We have some other family friends, that in the past couple years, I'm more likely to ask for them to help with pick up from school, etc.. For a while, we were paying the older sister in the family to babysit (even though the parents were driving, etc.). The family told us we didn't need to pay for a babysitter. Our son had become like family to them and they were happy to help. They are used to having the benefits of extended family in the area, whereas our family and our friend from last night are not. I was thinking today that, for a lot of people and especially my generation and before, picking up other peoples kids, having them go to other people's houses, asking for last minute help was pretty normal (in some communities and situations, I'm sure this is still normal today). But sometimes we either aren't comfortable with the community around us, don't know them that well or don't want to inconvenience others. I think the worry about inconveniencing others is something we should try to let go of.
Yes, we need to be respectful of the time and needs and situations of others. Yes, some people have trouble with boundaries and saying, "No". So maybe don't ask people if you know they would say yes to anything. For those friends though that you can, ask. I asked someone who I have a budding friendship with if she'd help me with my son's Halloween costume. She totally could have said no. I was half expecting it, or for her to charge me for her time (I did offer to pay). Not only did she do a wonderful job, she told me she prayed for my family while she was working on it. I was able to offer her some consolation and practical support, as we were able to be prayer partners for each other. She was grateful to help out, to do something out of the ordinary for her and to give of herself. Her kids are growing older, and my son's Halloween costume was her "opportunity to have someone wear a Halloween costume I made."
When we help and give of ourselves to others, we receive so much. I think sometimes we need to allow others to give to us as well. It benefits both the giver and the recipient. Don't feel guilty about asking for help. The worst that can happen is they say no. The gifts that could happen are numerous.